Fumigaclavine C
 8β isomer | |
| Names | |
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| IUPAC name
[(6aR,9S,10S)-7,9-Dimethyl-5-(2-methylbut-3-en-2-yl)-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-10-yl] acetate | |
| Other names
SM-1; (8β,9β)-2-(1,1-Dimethyl-2-propenyl)-6,8-dimethylergolin-9-ol acetate | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| KEGG | |
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C23H30N2O2 | |
| Molar mass | 366.505 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Fumigaclavine C is an ergoline alkaloid produced by Aspergillus fumigatus.[1]
Both 8α and 8β diastereomers (epimers) were named fumigaclavine C in scientific literature.[2]
Biosynthesis
[edit]The final step in the biosynthesis of the ergot alkaloid fumigaclavine C in fungi of the Trichocomaceae family is catalysed by the enzyme, fumigaclavine A dimethylallyltransferase:
The enzyme was characterised from Aspergillus fumigatus and produces the 8α stereoisomer shown.[3]
See also
[edit]References
[edit]- ↑ Ma, HY; Song, YC; Mao, YY; Jiang, JH; Tan, RX; Luo, L (2006). "Endophytic fungal metabolite fumigaclavine C causes relaxation of isolated rat aortic rings". Planta Medica. 72 (5): 387–92. doi:10.1055/s-2005-916235. PMID 16557450.
- ↑ Wallwey, Christiane; Li, Shu-Ming (2011-03-01). "Ergot alkaloids: structure diversity, biosynthetic gene clusters and functional proof of biosynthetic genes". Natural Product Reports. 28 (3): 496–510. doi:10.1039/C0NP00060D. ISSN 1460-4752. PMID 21186384.
- ↑ Unsöld IA, Li SM (January 2006). "Reverse prenyltransferase in the biosynthesis of fumigaclavine C in Aspergillus fumigatus: gene expression, purification, and characterization of fumigaclavine C synthase FGAPT1". ChemBioChem. 7 (1): 158–64. doi:10.1002/cbic.200500318. PMID 16397874.
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